Mill, whose real name is Robert Williams, pleaded with Brinkley to let him continue working. Mill said his career supports him, his mother, sister, son, and other friends and placed his monthly expenses at $80,000 to $90,000.
"It took me 15 years to get here, and this will be extremely damaging to my life," Mill said.
Brinkley referred to almost two years of probation violation hearings spent trying to reconcile the terms of his probation with Mill's burgeoning international concert schedule.
"You just don't get it," the judge said.
By the end of the hearing, the tall, thin rapper, dressed in a white shirt and tie and black pants, seemed resigned to what he knew was coming.
Not so his posse of more than a dozen people who seemed stunned as sheriff's deputies escorted him from the courtroom to be transported to the city's prison complex in the Northeast.
Several women left in tears and outside of court talked animatedly about injustice.
"He didn't do nothing wrong," protested one.
Mill will spend at least three months in prison and possibly the full six. When he gets out, he will have to start a new five-year period of probation.
Brinkley warned him not to make further concert plans without court approval.
When Mill said his schedule was "now booked up till December," Brinkley cut him off.
"I don't want to hear it, I don't care about it," the judge said.
Mill has been a regular in court for nearly two years, disputing the terms of his probation with Philadelphia probation officers and trying Brinkley's patience as she worked to accommodate his schedule.
Assistant District Attorney Noel DeSantis asked Brinkley to sentence Mill to five to 10 years in prison. She and probation officer Treas Underwood recited a litany of alleged violations.
Some had to do with scheduling problems, which required Mill to be in constant contact with Underwood while touring, providing details about his itinerary.
They also showed a photo of Mill, posing with four men, holding what appeared to be a semiautomatic pistol - Silver said it was a prop during a photo shoot - and Mill's insulting comments about DeSantis and Underwood on Twitter, some written while he was in the probation office.
DeSantis said one tweet referred to her as a "racist [expletive]" and attacked Underwood, who is African American, as being jealous that one of her probationers had become a famous and wealthy entertainer.
"He's asking me to send him to jail and that's what I'm going to ask for," DeSantis told Brinkley.
The final straw appeared to be when Brinkley heard that Mill had booked concerts between Thursday and Aug. 11, a time when she had ordered him to stop performing while she tried to resolve his probation problems.
Mill was supposed to have headlined a concert Friday night in Washington.
Said Brinkley: "He's not going to make that concert tonight."